Private foundations are attempting to move away from educational reform approaches based on model development. The limits of the "Johnny Appleseed" (sowing seed and moving on) mode of grantmaking are coming clear. Persistence--a willingness to commit resources to an issue or institution for 5 to 10 years--will need to be an operating principle in any new mode of strategic philanthropy, especially in an era of public fiscal constraint. As years of public policy implementation convey, change takes time, particularly when the targets are schools and school districts built on complex patterns of organizational and individual behavior. But, for foundations, persistence bumps against other, vital principles, such as leverage, maximum flexibility, stewardship, and pluralism. Three different Chicago (Illinois) foundations, the Chicago Community Trust, the Joyce Foundation, and the Woods Fund of Chicago, which have been funding Chicago school reform for over 7 years, offer clues as to the sources and nature of the dilemma created by persistence. Three figures and one table illustrate the discussion. (Contains 37 references.) (Author/SLD)